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WO2010042391A3 - Hiv integrase inhibitors - Google Patents

Hiv integrase inhibitors Download PDF

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Publication number
WO2010042391A3
WO2010042391A3 PCT/US2009/059306 US2009059306W WO2010042391A3 WO 2010042391 A3 WO2010042391 A3 WO 2010042391A3 US 2009059306 W US2009059306 W US 2009059306W WO 2010042391 A3 WO2010042391 A3 WO 2010042391A3
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
hiv
hiv integrase
inhibitors
integrase inhibitors
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2009/059306
Other languages
French (fr)
Other versions
WO2010042391A2 (en
Inventor
Richard C. A. Isaacs
Wayne J. Thompson
Peter D. Williams
Dai-Shi Su
Shankar Venkatraman
Mark W. Embrey
Thorsten E. Fisher
John S. Wai
David C. Dubost
Richard G. Ball
Eric J. Choi
Tao Pei
Sarah L. Trice
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Organon Pharma UK Ltd
Merck Sharp and Dohme LLC
Original Assignee
Merck Sharp and Dohme Ltd
Merck Sharp and Dohme LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Sharp and Dohme Ltd, Merck Sharp and Dohme LLC filed Critical Merck Sharp and Dohme Ltd
Priority to MX2011003637A priority Critical patent/MX2011003637A/en
Priority to EA201170537A priority patent/EA201170537A1/en
Priority to BRPI0920605A priority patent/BRPI0920605A8/en
Priority to CN2009801489012A priority patent/CN102239172A/en
Publication of WO2010042391A2 publication Critical patent/WO2010042391A2/en
Publication of WO2010042391A3 publication Critical patent/WO2010042391A3/en
Priority to IL212019A priority patent/IL212019A0/en
Priority to TN2011000151A priority patent/TN2011000151A1/en
Anticipated expiration legal-status Critical
Priority to ZA2011/02620A priority patent/ZA201102620B/en
Priority to MA33804A priority patent/MA32764B1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • AIDS & HIV (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

Compounds of Formula I are inhibitors of HIV integrase and inhibitors of HIV replication: (I), wherein X1, X2, Y, R1A, R1B, R2 and R3 are defined herein. The compounds are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset or progression of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se (or as hydrates or solvates thereof) or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.
PCT/US2009/059306 2008-10-06 2009-10-02 Hiv integrase inhibitors Ceased WO2010042391A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
MX2011003637A MX2011003637A (en) 2008-10-06 2009-10-02 Hiv integrase inhibitors.
EA201170537A EA201170537A1 (en) 2008-10-06 2009-10-02 HIV INTEGRASE INHIBITORS
BRPI0920605A BRPI0920605A8 (en) 2008-10-06 2009-10-02 COMPOUND OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PHARMACEUTICAL COMPOSITION, AND METHOD FOR THE TREATMENT OR PROPHYLAXIS OF HIV INFECTION OR FOR THE TREATMENT, PROPHYLAXIS, OR DELAY IN THE ONSET OR PROGRESSION OF AIDS IN A PATIENT IN NEED THEREOF.
CN2009801489012A CN102239172A (en) 2008-10-06 2009-10-02 Hiv integrase inhibitors
IL212019A IL212019A0 (en) 2008-10-06 2011-03-29 Hiv integrase inhibitors
TN2011000151A TN2011000151A1 (en) 2009-10-02 2011-03-30 Hiv integrase inhibitors
ZA2011/02620A ZA201102620B (en) 2008-10-06 2011-04-08 Hiv integrase inhibitors
MA33804A MA32764B1 (en) 2008-10-06 2011-05-02 HIV antigrade inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US19527108P 2008-10-06 2008-10-06
US61/195,271 2008-10-06

Publications (2)

Publication Number Publication Date
WO2010042391A2 WO2010042391A2 (en) 2010-04-15
WO2010042391A3 true WO2010042391A3 (en) 2010-06-03

Family

ID=41682332

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/US2009/059308 Ceased WO2010042392A2 (en) 2008-10-06 2009-10-02 Hiv integrase inhibitors
PCT/US2009/059306 Ceased WO2010042391A2 (en) 2008-10-06 2009-10-02 Hiv integrase inhibitors

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/US2009/059308 Ceased WO2010042392A2 (en) 2008-10-06 2009-10-02 Hiv integrase inhibitors

Country Status (22)

Country Link
US (2) US8513234B2 (en)
EP (1) EP2349276B1 (en)
JP (2) JP4880097B1 (en)
KR (1) KR20110066224A (en)
CN (1) CN102239172A (en)
AR (1) AR073769A1 (en)
AU (1) AU2009302663B2 (en)
BR (1) BRPI0920605A8 (en)
CA (1) CA2738814C (en)
CO (1) CO6382127A2 (en)
CR (1) CR20110184A (en)
DO (1) DOP2011000093A (en)
EA (1) EA201170537A1 (en)
EC (1) ECSP11010959A (en)
IL (1) IL212019A0 (en)
MA (1) MA32764B1 (en)
MX (1) MX2011003637A (en)
NI (1) NI201100069A (en)
PE (1) PE20110344A1 (en)
TW (1) TW201020251A (en)
WO (2) WO2010042392A2 (en)
ZA (1) ZA201102620B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11084832B2 (en) 2019-03-22 2021-08-10 Gilead Sciences, Inc. Bridged tricyclic carbamoylpyridone compounds and their pharmaceutical use
US11613546B2 (en) 2021-01-19 2023-03-28 Gilead Sciences, Inc. Substituted pyridotriazine compounds and uses thereof
US11697652B2 (en) 2020-02-24 2023-07-11 Gilead Sciences, Inc. Tetracyclic compounds and uses thereof
US12024528B2 (en) 2022-04-06 2024-07-02 Gilead Sciences, Inc. Bridged tricyclic carbamoylpyridone compounds and uses thereof
US12421235B2 (en) 2020-09-30 2025-09-23 Gilead Sciences, Inc. Bridged tricyclic carbamoylpyridone compounds and uses thereof

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8283366B2 (en) 2010-01-22 2012-10-09 Ambrilia Biopharma, Inc. Derivatives of pyridoxine for inhibiting HIV integrase
WO2014008636A1 (en) * 2012-07-11 2014-01-16 Merck Sharp & Dohme Corp. Macrocyclic compounds as hiv integrase inhibitors
CN102936188B (en) * 2012-11-19 2015-07-15 湖北吉和昌化工科技有限公司 Propynol glycidyl ether synthesis method
US9493479B2 (en) 2013-04-16 2016-11-15 Merck Sharp & Dohme Corp. Substituted pyrido[1,2-a]pyrazines as HIV integrase inhibitors
CN107722106A (en) * 2016-08-11 2018-02-23 重庆大学 HIV inhibitors
CN111454214B (en) * 2020-05-27 2023-04-07 龙曦宁（上海）医药科技有限公司 Synthetic method of 2-methoxy-1-pyrimidineethylamine hydrochloride

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005061501A2 (en) * 2003-12-12 2005-07-07 Merck & Co., Inc. Process for preparing hexahydropyrimido[1,2-a]azepine-2-carboxylates and related compounds
WO2006060225A2 (en) * 2004-11-23 2006-06-08 Merck & Co., Inc. Process for asymmetric synthesis of hexahydropyrimido[1,2-a] azepine-2-carboxamides and related compounds
WO2006103399A1 (en) * 2005-03-31 2006-10-05 Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa Hiv integrase inhibitors

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ES2383262T3 (en) 2001-08-10 2012-06-19 Shionogi & Co., Ltd. Antiviral agent
JP4351053B2 (en) 2001-10-26 2009-10-28 イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー Dihydroxypyrimidine carboxamide HIV integrase inhibitor
EP1441735B1 (en) 2001-10-26 2006-02-22 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase
JP4523281B2 (en) 2002-01-17 2010-08-11 メルク・シャープ・エンド・ドーム・コーポレイション Hydroxynaphthyridinone carboxamides useful as HIV integrase inhibitors
JP4733986B2 (en) * 2002-12-27 2011-07-27 イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー Tetrahydro-4H-pyrido [1,2-a] pyrimidines and related compounds useful as HIV integrase inhibitors
US7135467B2 (en) 2003-01-13 2006-11-14 Bristol-Myers Squibb Company HIV integrase inhibitors
US7037908B2 (en) 2003-04-24 2006-05-02 Bristol-Myers Squibb Company HIV integrase inhibitors
TW200510425A (en) 2003-08-13 2005-03-16 Japan Tobacco Inc Nitrogen-containing fused ring compound and use thereof as HIV integrase inhibitor
TW200526635A (en) 2003-12-22 2005-08-16 Shionogi & Co Hydroxypyrimidinone derivative having HIV integrase inhibitory activity
DE602005012069D1 (en) 2004-04-06 2009-02-12 Novartis Vaccines & Diagnostic INHIBITORS OF MITOTIC KINESINE
US7273859B2 (en) 2004-05-12 2007-09-25 Bristol-Myers Squibb Company HIV integrase inhibitors: cyclic pyrimidinone compounds
US7115601B2 (en) 2004-05-18 2006-10-03 Bristol-Myers Squibb Company HIV integrase inhibitors
US7192948B2 (en) 2004-05-28 2007-03-20 Bristol-Myers Squibb Company Bicyclic heterocycles as HIV integrase inhibitors
US7173022B2 (en) 2004-05-28 2007-02-06 Bristol-Myers Squibb Company Bicyclic heterocycles as HIV integrase inhibitors
US7176196B2 (en) 2004-05-28 2007-02-13 Bristol-Myers Squibb Company Bicyclic heterocycles as HIV integrase inhibitors
US7157447B2 (en) 2004-05-28 2007-01-02 Bristol-Myers Squibb Company Bicyclic heterocycles as HIV integrase inhibitors
US7494984B2 (en) 2005-08-31 2009-02-24 Bristol-Myers Squibb Company Substituted imidazo[1,2-a]pyrimidines as HIV viral DNA integrase inhibitors
US7897592B2 (en) 2005-11-15 2011-03-01 Bristol-Myers Squibb Company HIV integrase inhibitors
WO2007058646A1 (en) 2005-11-15 2007-05-24 Bristol-Myers Squibb Company Hiv integrase inhibitors: cyclic pyrimidinone compounds
US7902182B2 (en) 2005-11-16 2011-03-08 Bristol-Myers Squibb Company HIV integrase inhibitors
US8039458B2 (en) 2005-11-17 2011-10-18 Bristol-Myers Squibb Company HIV integrase inhibitors
WO2007064316A1 (en) 2005-11-30 2007-06-07 Bristol-Myers Squibb Company Bicyclic heterocycles as hiv integrase inhibitors
WO2007143446A1 (en) 2006-05-30 2007-12-13 Bristol-Myers Squibb Company Spiro-condensed heterotricyclic compounds as hiv integrase inhibitors
US7893055B2 (en) 2006-06-28 2011-02-22 Bristol-Myers Squibb Company HIV integrase inhibitors

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005061501A2 (en) * 2003-12-12 2005-07-07 Merck & Co., Inc. Process for preparing hexahydropyrimido[1,2-a]azepine-2-carboxylates and related compounds
WO2006060225A2 (en) * 2004-11-23 2006-06-08 Merck & Co., Inc. Process for asymmetric synthesis of hexahydropyrimido[1,2-a] azepine-2-carboxamides and related compounds
WO2006103399A1 (en) * 2005-03-31 2006-10-05 Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa Hiv integrase inhibitors

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11084832B2 (en) 2019-03-22 2021-08-10 Gilead Sciences, Inc. Bridged tricyclic carbamoylpyridone compounds and their pharmaceutical use
US11548902B1 (en) 2019-03-22 2023-01-10 Gilead Sciences, Inc. Bridged tricyclic carbamoylpyridone compounds and their pharmaceutical use
US12227520B2 (en) 2019-03-22 2025-02-18 Gilead Sciences, Inc. Bridged tricyclic carbamoylpyridone compounds and their pharmaceutical use
US11697652B2 (en) 2020-02-24 2023-07-11 Gilead Sciences, Inc. Tetracyclic compounds and uses thereof
US12122776B2 (en) 2020-02-24 2024-10-22 Gilead Sciences, Inc. Tetracyclic compounds and uses thereof
US12421235B2 (en) 2020-09-30 2025-09-23 Gilead Sciences, Inc. Bridged tricyclic carbamoylpyridone compounds and uses thereof
US11613546B2 (en) 2021-01-19 2023-03-28 Gilead Sciences, Inc. Substituted pyridotriazine compounds and uses thereof
US11897892B2 (en) 2021-01-19 2024-02-13 Gilead Sciences, Inc. Substituted pyridotriazine compounds and uses thereof
US12024528B2 (en) 2022-04-06 2024-07-02 Gilead Sciences, Inc. Bridged tricyclic carbamoylpyridone compounds and uses thereof
US12054496B2 (en) 2022-04-06 2024-08-06 Gilead Sciences, Inc. Bridged tricyclic carbamoylpyridone compounds and uses thereof

Also Published As

Publication number Publication date
EP2349276B1 (en) 2019-11-27
CR20110184A (en) 2011-06-08
JP2012504648A (en) 2012-02-23
WO2010042392A3 (en) 2010-06-03
IL212019A0 (en) 2011-06-30
MA32764B1 (en) 2011-11-01
US20100087419A1 (en) 2010-04-08
EP2349276A2 (en) 2011-08-03
ZA201102620B (en) 2011-12-28
CA2738814A1 (en) 2010-04-15
TW201020251A (en) 2010-06-01
JP4880097B1 (en) 2012-02-22
ECSP11010959A (en) 2011-05-31
JP2012036207A (en) 2012-02-23
CO6382127A2 (en) 2012-02-15
PE20110344A1 (en) 2011-06-22
MX2011003637A (en) 2011-04-27
BRPI0920605A8 (en) 2016-04-26
CN102239172A (en) 2011-11-09
KR20110066224A (en) 2011-06-16
DOP2011000093A (en) 2011-07-15
WO2010042391A2 (en) 2010-04-15
US20130338141A1 (en) 2013-12-19
NI201100069A (en) 2012-08-08
EA201170537A1 (en) 2011-12-30
WO2010042392A2 (en) 2010-04-15
AU2009302663A1 (en) 2010-04-15
JP5600311B2 (en) 2014-10-01
US8513234B2 (en) 2013-08-20
AU2009302663B2 (en) 2012-11-08
BRPI0920605A2 (en) 2015-12-22
AR073769A1 (en) 2010-12-01
CA2738814C (en) 2014-01-28

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